This contribution aims to provide a framework for viewing the fragility of employability and potentially fruitful routes for making employability more sustainable. A second goal, is to inspire readers with examples from the Netherlands, to create and test promising interventions, so that a broad set of effective interventions becomes available for each route presented. In the first part of this contribution sustainable employability is introduced as ‘a constant match between what a worker is willing and able to do and what the work demands and provides’. Employability is ‘fragile’ due to two mechanisms: skills obsolescence and motivation erosion. Both mechanisms affect all workers, but to differing degrees. We distinguish three routes to avoid adverse effects of both mechanisms: development, job redesign, and mobility. Identifying the route that is best in terms of sustainable employability depends on a clear diagnosis of the nature of the skills obsolescence and motivation erosion mechanisms. Although routes are taken by individual workers, employers have the responsibility to both accommodate and accompany a worker on finding and taking his route to sustainable employability. In the second part of this contribution we present the “Dutch case” of sustaining employability. First, we show the fragility of workers who lack basic qualification. Next, we present examples from Dutch practice that show how the dynamic perspective is applied and what different routes workers can take toward sustainable employability. Although these examples are all Dutch, they can easily be transferred to other countries.